Vacation Rentals & Apartments in Kailua

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672 apartments

Amazing 2BR Condo in The Cliffs

Princeville condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared indoor pool Beach or lakeside relaxation

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$295

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A201 VISTA WAIKOLOA DELUXE - OCEAN VIEW-2 BDR

Waikoloa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Feels like home--but warm and sunny!” We traveled with family and were happy to be able to rent two units next door to each other (A201 & A202). We really loved the condos--the colors, furniture, and artwork really gave the units an island feel. The spacious units with cozy furnishings, comfortable beds, beach gear, well-stocked kitchen, and convenient location made our stay especially relaxing--just 10-15 min walk to shops, marketplace, and a-Bay beach. We cooked quite a bit, so the availability of olive oil, vinegars of all flavors, butter, spices, and other kitchen condiments and accoutrement's were especially appreciated. You even have the choice of brewed coffee or espresso! To save money and get more selection, rather than do most of our shopping at the Queen's marketplace, we stocked up at Costco in Kona and Foodland in Waimea. We contributed to the pantry and fridge by leaving goodies for the next visitors (just as the previous visitors had done). The 2nd floor was nice because we could keep the windows open to let the breeze through rather than use the air-conditioning. With the windows open, we were all up at 6am to the sound of squawking birds and noisy buses and trucks. Since we wanted to go running before it got too hot, the sound of birds in the morning was better than the buzzer of an alarm clock. Although we were surprised by the road noise (it was definitely enough to wake us up when the windows were open), it wasn't enough to discourage us from staying here. The other choice would be to stay on the golf course side of the building that doesn't have the sunset view and can get really windy). A202 is a bit larger (3 bathrooms) than a201, but both units had their own charm. 201 has brighter bedrooms and a bigger master bedroom, but 202 has a bigger patio table that easily seated 8 and a brighter kitchen. Last, but not least--Sylvia was a wonderful host!

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$401

Kaanapali Shores panoramic ocean - view sleeps 4

Ka'anapali apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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$344

Kamaole Sands 7-110 South Kihei, Maui, Sleep 4

Kihei apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$263

“Clean, modern, wonderful place to stay” When we arrived we were pleasantly surprised at how beautiful and clean the condo was. It was like being home. Beautiful grounds, pool, and easy access to beach.

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$205

2 bedroom\2 bath condo located in heart of Lahaina

Lahaina apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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$544

More Aloha For Your Money!

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Second stay in this lovely condo...” We stayed in this condo two years ago and was impressed with the price and comforts of home that we decided to stay a second time. This condo is still the best value in Kihei. We enjoyed the ocean view from the lanai every morning and went boogie boarding and snorkeling at Kam II everyday. Snorkeling was amazing. We saw beautiful fish and turtles each time. The complex is well maintained and clean. We even used the outdoor grill by the pool and it looked brand new. We will definitely be back.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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$182

Maui Parkshore 3rd Floor *Ocean View* 2 BR/2 Bath

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect location, great view” Unit was clean and comfortable for four adults and a baby. Steps from a fabulous beach. Short walk to shops and restaurants. All the amenities of home. Loved our stay. Can't wait to go back.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$315

WAIKIKI 1BD CRN,FREE PKG,WIFI,NETFLIX,YOU TUBE, BEACH ITEMS,CALLS,

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

“Great” We arrived late after 3 weeks in usa mainland, where we did not stop. Getting our keys and into theunit was so easy. It was so close to get to everything from the unit. We had a family of five and with the sofa bed out it was quite tight. Maybe not so many little tables and trinkets. But that would be our only complaint. Everything was just as the photos showed and a great place for a family. We went and did food shopping at safeway, but then found Wallmart cheaper. Thanks heaps for having us

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$194

Kamaole Beach Royale 1 Bedroom Seaviews

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 6 minutes

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$258

Surfrider Unobstructed Seaviews 1Bedroom

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 6 minutes

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$258

**Makaha Beautiful Top floor 2bdrm Condo with views- Air Con // Wifi

Makaha apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Very enjoyable, relaxing and peaceful amongst the local people not in the rat race of touristy Waikiki.” We did not rent a car and used the local bus system to travel everywhere which was great but time consuming. The accommodation is at least an hour from Honolulu and Waikiki so travelling on a bus late at night is not ideal, however the bus does stop outside the condo complex. The condo facilities are comfortable with access to 2 pools, it is on the 3rd floor with stair access only which is hard with heavy luggage, however being higher up means there are sea views and the benefit of fresh breezes. We found the owner friendly and approachable.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$114

Cottage on the Beach, Romantic, Oahu North Shore Mokuleia (Licensed!)

Waialua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“The sound of the waves, right outside your door, are like a lull” We had a "rough time" getting here (mechanical problems with the plane, canceled flight, etc.) but the cottage soothed our tired souls! We found the drum of the waves to be the best lullaby and the fresh air and abundant sunshine to renew our spirits. We appreciated the personal art on the walls and the large open space. For folks who enjoy cooking with local produce, the well stocked kitchen, the large number of pots/pans/utensils, and the full sized refrigerator are perfect. There was plenty of hot water in the shower (and good water pressure!), the furniture was comfortable (brought back memories of beach houses from our childhood), and the large counter surface in the "dressing room" was perfect for all of our "stuff". We used the outdoor patio table for several breakfasts and dinners, watched a neighbor vacationer fish from the sea wall, and took daily walks on the nearly deserted beach. There were many informative books in the cottage along with maps, Dvds, etc. We used the guide books but were too busy enjoying Oahu to need any other form of entertainment! Although we have traveled extensively in the past few years, this was our first trip to Hawaii. We have already recommended the cottage to family and friends - thank you, Peter, for sharing your wonderful home.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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$338

Kahana Sunset 2 BR Condo, Ocean View, Great Beach

Lahaina apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“A decision you won't regret!” We recently stayed in E-6 and absolutely loved it. From the ease of being able to book the condo to the great service we received from Mike. He was always willing to help with all and any questions I had with not only the condo, but our entire trip. The pictures do not do this unit justice, everything worked out better than could be expected! The beach is peaceful and only a short walk from the front door, full of beautiful fish and turtles. The condo is a very short drive from Lahaina and only a couple blocks from a grocery store. If you are looking for a great getaway with all the amenities of home, this is exactly what your looking for! Can't wait to go back and definitely will be staying at Kahana Sunset!!

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$344

Seaviews Kanani 1 bedroom

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“A truly wonderful experience that keeps you coming back.” I have done a fair amount of traveling in my lifetime and have chosen to go to Kihei, Hawaii two out of the last three years for vacation. This year, I expect to return again. This is the perfect rental, it can be whatever you want it to be. In the morning we sit outdoors having coffee, watching the ocean glicin, people surfing and whales jumping. The accomodation is centrally located you can walk the beaches,swim in the pool outside your door or walk to the shops and restaurants. The accomodations are great and there are so many modern features and amenities. It is more than I ever expected and the price is reasonable. Carolyn is one of the best managers/hostess. Carolyn is very friendly and helpful. She goes out of her way to make sure that her vacationers' have what they like and more! I would recommend this condo to everyone, but please don't take my spot!

Responds fast! avg. 2 hours 6 minutes

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$258

New! Oceanfront Ground Floor 2/2 by the Beach

Lahaina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$607

Maui Kamaole B101 Hawaiian Dream

Kihei apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$373

QUIET condo Across from Charley Young Beach, one of Maui's Best !!!!

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Awesome” Everything was perfect thank you kehei for such a memorable stay. We will be back the Maui vista was literally accross the street from a beautiful beach I recommend highly

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$287

Great Ocean Views! 2007 Built Penthouse at Kahaluu

Kailua-Kona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$343

WOW-New 2bd MAUI ELDORADO Ocean & Golf View Corner

Ka'anapali apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Wonderful large modern view condo in Kaanapali” Great service, document outlining condo, restaurants, activities, etc. Very large condo for Kaanapali, fantastic views, very well appointed kitchen, boogie boards, fins, snorkels, very nice bathrooms with large showers, lots of towels, etc. Kaanapali is great location, walking distance to restaurants and shops, near Lahaina which has many restaurants, stores, etc. We liked the great views, spaciousness of condo, location in Kaanapali

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$573

Beautiful condo in the heart of Lahaina Maui

Lahaina apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Paradise Found” Thank you for providing a beautiful condo for us to stay in. The unit was in the perfect location at the resort. We loved seeing the lights from the garden pool outside of our bedroom at night. The furnishings are absolutely beautiful and the unit was very clean! We loved the spa shower! We could not have asked for a more perfect place to spend our vacation. We only wish that we had booked a longer trip. We will definitely be back. We really appreciated your recomendations on where to eat and what to see while visiting Maui. Star noodle is our new favorite restaurant! The location of the resort itself was perfect. We loved being able to walk to new restaurants every night, except for the nights we cooked in! We really enjoyed the Bbq's and the fully stocked kitchen. We were also able to find free parking every night on the street out front. Thank you again for lettings us stay in your beautiful condo, we will be back!

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$457

Eco-Friendly Condo Located in the Heart of Kihei

Kihei house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Well equipped and maintained, comfortable and easy access to beach, food and shopping.” This was my second stay at this lovely 1 BR condo in Kihei and I enjoyed it even more. The location is great, just across S Kihei Rd from the beach at the north end of Kamaole Beach #1. You can walk on the beach all the way to Ulua Beach if you want. The place is amazingly well equipped. All you need to cook and toys for the beach. This time, I even discovered two yoga mats in covers and two yoga blocks to go with them. Perfect for home yoga or taking them to the beach yoga classes that sometime happen. It is also possible to walk to good food and even the grocery store. The building has a great pool for afternoon cooling and laundry facilities are available on site. There is a bit of a view of the ocean from the lanai, but the general vista of palm trees and tropical vegetation in the neighboring buildings was quite nice. Never used the AC, screens and fans kept things comfortable. Finally the electronics were great, big screen and lots of music and video service choices.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$509

Oceanfrt 2br Condo-Halii Kai 14C-Oceanfront & newly renovated & Hilton Passes

Waikoloa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Best Big Island Experience - Unit 14C” We decided to check out Halii Kai condo on our third trip to the Big Island. The condo complex was so beautifully maintained, peaceful and provides a very residential feel. Unit 14C was beautifully decorated and very well furnished. The kitchen was well equipped and came with all high end appliances. Peggy even provided bottled water and a six pack of Heineken in the refrigerator for us. We had plenty of linen, pillow, etc. to make us feel completely at home. We were able to use the beach chairs and body boards during our stay. We brought our own snorkeling equipment. Next time, we might try out the tennis and basketball courts since Peggy provide racquets and balls too. From the lanai, we had a beautiful ocean front view. We watched the whale cavorting in the water all week. There is access to the Trail by the Sea but the closest beach access are those by the Hilton or the Marriott. It was a pleasure to work with Peggy through out the process. We cannot wait to come back for another relaxing vacation at Halii Kai, Unit 14C.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$516

VISTA WAIKOLOA F205 - LUXURY- GOLF DISCOUNT- VIEWS - 2 MASTER SUITES

Waikoloa apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great place, great golf view!!” Loved the location of this condo looking over the golf course and towards the mountains. Everything is so close, shopping, the beach, etc. It is beautifully decorated to feel so Hawaiian, and it is very comfortable.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$401

Oceanview 2Br Halii Kai Condo12A-Golf Course & Ocean View & Hilton Passes Incl

Waikoloa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Halii Kai 12a was just like home...but better!” We stayed at Halii Kai Condo 12a for 12 days in September 2013. It was fabulous! We are well-seasoned travelers and would have to rate this stay in the top 5 we've ever had. The condo is like a home away from home. Peggy has everything you could possibly need including a fully stocked & well-equipped kitchen, coolers, games, beach towels, full drawer of Dvds for rainy days, Hawaii travel guides, etc. The location is fabulous with ocean views from the lanai just like in the pictures. The condo facility is quiet and well-maintained with a nice pool and small gym. Peggy herself was wonderful to deal with and was very attentive to our requests and needs. She asked us for recommendations or suggestions on how to improve and honestly, we just don't have any because she has already thought of everything. If you are looking for a condo stay in the Waikoloa area you should definitely stay here as you will not be disappointed!

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$516

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$138

Breathtaking Oceanview Paradise at Malulani Green Haven in Kona

Kailua-Kona house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$458

Maui Banyan Condo - Deluxe 2 Bedroom Retreat

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Absolutely the best condo to stay in Maui” This is the second time that we have stayed here and we always book this place. Very clean, nice decor, and everything you will need on vacation. There is a beautiful beach steps away from the condo, along with restaurants, and shopping, all very close.

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$265

ELEGANT BEACH HOME POOL & VIEW PERFECT LOCATION

Kihei house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$4,403

Poipu Oceanfront Dream Getaway!

Koloa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$304

“Location, Location, Location!” The condo is just a short walk to the beach which we enjoyed daily. It's close to many great restaurants offering a variety of cuisines. We caught the bus right outside the door for travel to all of our sightseeing destinations. With a grocery store just a few blocks away we had easy access to the things we needed to prepare most of our meals in the kitchen. We loved having breakfast and coffee out on the lanai each morning looking out at the ocean view. The condo was clean and comfortable. The manager was quick to respond. We look forward to going back!

Responds fast! avg. 1 hour 47 minutes

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$184

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$224

“"Lovely"” We stayed at Suite Aloha in September for 11 days. The room was spacious, airy and very comfortable. There was a huge ceiling fan to cool the entire room throughout the day and night. We were awakened by the sweet fragrance of plumeria as it floated through the windows every morning. Lovely! Sabine thought of everything to make our stay comfortable. We were welcomed with fresh fruit and a Beautiful arrangement of fresh Hawaiian flowers. There were beach items available for us to use including a beach umbrella, chairs, mats and beach bag. The location was ideal. We could easily walk to Kailua Beach or to Kailua town. Kailua town has plenty of upscale shops and restaurants. There was even a brand new Target there. We would definitely stay there again. It was lovely!

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$108

Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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$224

2 Adjoining Suites -- POSH AND LAVISH -- Direct Ocean Views

Honolulu apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$796

Garden Cottage

Kealakekua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$205

Surf and Racquet 1201 2/2 Oceanfront

Kailua-Kona condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“sitting on the huge lanai on the ocean listening to the waves crash was wonderful” Kim of Keauhou Property Management impressed me the most. He answered my calls and questions promptly. When we left as did not need 2 bedroom and moved to another rental it was awful, Called Kim and he managed to find me a couple of rentals that covered our stay. He is my hero and highly recommend him and his company for their GREAT customer service. The property was great too, nice amenities and prefer this area now verses up the road closer to the hustle bustle but close enough to go.

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$195

Surf and Racquet 5102 2/2 oceanfront

Kailua-Kona condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Shared indoor pool, Beach or lakeside relaxation

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Price per night from

$189

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